2,2-dimethyl-3-(p-toluenesulfonamido)-1-propanol p-toluenesulfonate | 79201-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-dimethyl-3-(p-toluenesulfonamido)-1-propanol p-toluenesulfonate
• 英文别名: [2,2-Dimethyl-3-[(4-methylphenyl)sulfonylamino]propyl] 4-methylbenzenesulfonate
• CAS: 79201-17-5
• 化学式: C₁₉H₂₅NO₅S₂
• 分子量: 411.543
• InChiKey: XCUBHYJVFMHFOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-3-(p-toluenesulfonamido)-1-propanol p-toluenesulfonate 在 氢化钾 作用下， 以 叔丁醇 为溶剂， 反应 12.3h， 以87.7%的产率得到3,3-dimethyl-1-tosylazetidine
  参考文献：
  名称：

  Enamines of 3,3-dimethylazetidine

  摘要：

  DOI：

  10.1021/jo00337a016
• 作为产物：
  描述：

  2-氰基-2-甲基丙酸乙酯 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 49.0h， 生成 2,2-dimethyl-3-(p-toluenesulfonamido)-1-propanol p-toluenesulfonate
  参考文献：
  名称：

  Enamines of 3,3-dimethylazetidine

  摘要：

  DOI：

  10.1021/jo00337a016

文献信息

• THOMPSON, H. W.;SWISTOK, J., J. ORG. CHEM., 1981, 46, N 24, 4907-4911
  作者：THOMPSON, H. W.、SWISTOK, J.

  DOI：——

  日期：——
• Novel Acetylcholine and Carbamoylcholine Analogues: Development of a Functionally Selective α₄β₂ Nicotinic Acetylcholine Receptor Agonist
  作者：Camilla P. Hansen、Anders A. Jensen、Jeppe K. Christensen、Thomas Balle、Tommy Liljefors、Bente Frølund

  DOI：10.1021/jm701625v

  日期：2008.12.11

  A series of carbamoylcholine and acetylcholine analogues were synthesized and characterized pharmacologically at neuronal nicotinic acetylcholine receptors (nAChRs). Several of the compounds displayed low nanomolar binding affinities to the alpha(4)beta(2) nAChR and pronounced selectivity for this subtype over alpha(3)beta(4), alpha(4)beta(4), and alpha(7) nAChRs. The high nAChR activity of carbamoylcholine analogue 5d was found to reside in its R-enantiomer, a characteristic most likely true for all other compounds in the series. Interestingly, the pronounced alpha(4)beta(2) selectivities exhibited by some of the compounds in the binding assays translated into functional selectivity. Compound 5a was a fairly potent partial alpha(4)beta(2) nAChR agonist with negligible activities at the alpha(3)beta(4) and alpha(7) subtypes, thus being one of the few truly functionally selective alpha(4)beta(2) nAChR agonists published to date. Ligand-protein docking experiments using homology models of the amino-terminal domains of alpha(4)beta(2) and alpha(3)beta(4) nAChRs identified residues Val 111(beta(2))/Ile 113(beta(4)), Phe 119(beta(2))/Gln 121(beta(4)), and Thr155(alpha(4))/Ser 150(alpha(3)) as possible key determinants of the alpha(4)beta(2)/alpha(3)beta(4)-selectivity displayed by the analogues. 4
• Enamines of 3,3-dimethylazetidine
  作者：Hugh W. Thompson、Joseph Swistok

  DOI：10.1021/jo00337a016

  日期：1981.11